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Name	Naratriptan	EINECS	N/A
CAS No.	121679-13-8	Density	1.227 g/cm³
PSA	73.58000	LogP	3.47840
Solubility	N/A	Melting Point	170-171°
Formula	C₁₇H₂₅N₃O₂S	Boiling Point	541.3 °C at 760 mmHg
Molecular Weight	335.47	Flash Point	281.2 °C
Transport Information	N/A	Appearance	N/A
Safety		Risk Codes	N/A
Molecular Structure		Hazard Symbols	N/A
Synonyms	N-Methyl-3-(1-methyl-4-piperidyl)indole-5-ethanesulfonamide;Naratriptan(Amerge);	Article Data	11

Naratriptan Synthetic route

: 894351-87-2
N-methyl-2-[1-benzyl-3-(1-methylpiperidin-4-yl)-1H-indol-5-yl]ethanesulfonamide

: 121679-13-8
naratriptan

Conditions

Conditions	Yield
With ammonia; sodium In tetrahydrofuran for 0.166667h;	84%
Stage #1: N-methyl-2-[1-benzyl-3-(1-methylpiperidin-4-yl)-1H-indol-5-yl]ethanesulfonamide With hydrogen; acetic acid; palladium 10% on activated carbon at 25℃; under 724.026 Torr; Stage #2: With ammonia In water at 10℃; pH=7.5 - 8.5;

: 639008-15-4
2-[3-(1-methylpiperidin-4-yl)-1H-indol-5-yl]ethanesulfonic acid benzylmethylamide

: 121679-13-8
naratriptan

Conditions

Conditions	Yield
With sodium In tetrahydrofuran; ammonia at -78℃; for 0.75h;	80%

: 121679-20-7
N-methyl-2-[3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indol-5-yl]ethanesulfonamide

: 121679-13-8
naratriptan

Conditions

Conditions	Yield
With hydrogen; palladium 10% on activated carbon In ethanol at 25 - 35℃; Product distribution / selectivity;	73.3%
With hydrogen; palladium 10% on activated carbon In ethanol; N,N-dimethyl-formamide at 25 - 35℃; under 2206.72 Torr; for 2h; Product distribution / selectivity;	72.7%
With 5% Pd(II)/C(eggshell); hydrogen; acetic acid In methanol; water at 25 - 35℃; under 6840.46 - 7600.51 Torr; Reactivity; Reagent/catalyst; Solvent; Time;	64%

: 1-benzyl-1-methyl-4-[5-(2-methylsulfamoyl-ethyl)-1H-indol-3-yl]-piperidinium bromide

A: 121679-13-8
naratriptan

B: 220392-03-0
2-[3-(1-benzyl-piperidin-4-yl)-1H-indol-5-yl]-ethanesulfonic acid methylamide

Conditions

Conditions	Yield
With lithium triamylborohydride In tetrahydrofuran for 26h; dequaternisation; Heating;	A n/a B 44%

: 1-methyl-4-[5-(2-methylsulfamoyl-ethyl)-1H-indol-3-yl]-1-(1-phenyl-ethyl)piperidinium bromide

A: 121679-13-8
naratriptan

B: 220392-08-5
2-{3-[1-(1-phenyl-ethyl)-piperidin-4-yl]-1H-indol-5-yl}-ethanesulfonic acid methylamide

Conditions

Conditions	Yield
With L-Selectride In tetrahydrofuran at 60℃; for 22h; dequaternisation; Title compound not separated from byproducts;

: 894351-85-0
2-(1-benzyl-1H-indol-5-yl)ethanesulfonic acid methylamide

: 121679-13-8
naratriptan

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 75 percent / trifluoroacetic acid; acetic acid / 1 h / 100 °C 2: 74 percent / H2 / 10 percent Pd/C / tetrahydrofuran / 4 h / 20 °C / 3750.3 Torr 3: 84 percent / Na; liquid NH3 / tetrahydrofuran / 0.17 h View Scheme
Multi-step reaction with 3 steps 1.1: potassium hydroxide / methanol / 8 h / 60 - 65 °C 2.1: trifluoroacetic acid / dichloromethane / 0.17 h / 25 °C 2.2: 25 - 30 °C 2.3: 10 - 15 °C 3.1: hydrogen; acetic acid / palladium 10% on activated carbon / 25 °C / 724.03 Torr 3.2: 10 °C / pH 7.5 - 8.5 View Scheme
Multi-step reaction with 2 steps 1: potassium hydroxide / methanol / 8 h / 60 - 65 °C 2: hydrogen; ethanol; triethylsilane / palladium 10% on activated carbon / ethanol / 25 - 30 °C View Scheme

: 894351-84-9
2-(1-benzyl-1H-indol-5-yl)ethenesulfonic acid methylamide

: 121679-13-8
naratriptan

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 84 percent / H2 / 10 percent Pd/C / methanol / 2 h / 20 °C / 3750.3 Torr 2: 75 percent / trifluoroacetic acid; acetic acid / 1 h / 100 °C 3: 74 percent / H2 / 10 percent Pd/C / tetrahydrofuran / 4 h / 20 °C / 3750.3 Torr 4: 84 percent / Na; liquid NH3 / tetrahydrofuran / 0.17 h View Scheme

: 894351-86-1
2-[1-benzyl-3-(1-methyl-1,2,3,6-tetrahydro-pyridin-4-yl)-1H-indol-5-yl]-ethanesulfonic acid methylamide

: 121679-13-8
naratriptan

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 74 percent / H2 / 10 percent Pd/C / tetrahydrofuran / 4 h / 20 °C / 3750.3 Torr 2: 84 percent / Na; liquid NH3 / tetrahydrofuran / 0.17 h View Scheme
With triethylsilane; ethanol; hydrogen; palladium 10% on activated carbon In ethanol at 25 - 30℃;
Multi-step reaction with 2 steps 1.1: trifluoroacetic acid / dichloromethane / 0.17 h / 25 °C 1.2: 25 - 30 °C 1.3: 10 - 15 °C 2.1: hydrogen; acetic acid / palladium 10% on activated carbon / 25 °C / 724.03 Torr 2.2: 10 °C / pH 7.5 - 8.5 View Scheme

: 63263-84-3
N-benzylindoline-5-carboxaldehyde

: 121679-13-8
naratriptan

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1.1: 75 percent / DDQ / CH2Cl2 / 3 h / 0 °C 2.1: t-BuOK / tetrahydrofuran / 1 h / -78 °C 2.2: 73 percent / tetrahydrofuran / -78 - 0 °C 3.1: 84 percent / H2 / 10 percent Pd/C / methanol / 2 h / 20 °C / 3750.3 Torr 4.1: 75 percent / trifluoroacetic acid; acetic acid / 1 h / 100 °C 5.1: 74 percent / H2 / 10 percent Pd/C / tetrahydrofuran / 4 h / 20 °C / 3750.3 Torr 6.1: 84 percent / Na; liquid NH3 / tetrahydrofuran / 0.17 h View Scheme

Yield

Multi-step reaction with 6 steps
1.1: 75 percent / DDQ / CH2Cl2 / 3 h / 0 °C
2.1: t-BuOK / tetrahydrofuran / 1 h / -78 °C
2.2: 73 percent / tetrahydrofuran / -78 - 0 °C
3.1: 84 percent / H2 / 10 percent Pd/C / methanol / 2 h / 20 °C / 3750.3 Torr
4.1: 75 percent / trifluoroacetic acid; acetic acid / 1 h / 100 °C
5.1: 74 percent / H2 / 10 percent Pd/C / tetrahydrofuran / 4 h / 20 °C / 3750.3 Torr
6.1: 84 percent / Na; liquid NH3 / tetrahydrofuran / 0.17 h
View Scheme

: 63263-88-7
1-benzyl-1H-indole-5-carbaldehyde

: 121679-13-8
naratriptan

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1.1: t-BuOK / tetrahydrofuran / 1 h / -78 °C 1.2: 73 percent / tetrahydrofuran / -78 - 0 °C 2.1: 84 percent / H2 / 10 percent Pd/C / methanol / 2 h / 20 °C / 3750.3 Torr 3.1: 75 percent / trifluoroacetic acid; acetic acid / 1 h / 100 °C 4.1: 74 percent / H2 / 10 percent Pd/C / tetrahydrofuran / 4 h / 20 °C / 3750.3 Torr 5.1: 84 percent / Na; liquid NH3 / tetrahydrofuran / 0.17 h View Scheme

Yield

Multi-step reaction with 5 steps
1.1: t-BuOK / tetrahydrofuran / 1 h / -78 °C
1.2: 73 percent / tetrahydrofuran / -78 - 0 °C
2.1: 84 percent / H2 / 10 percent Pd/C / methanol / 2 h / 20 °C / 3750.3 Torr
3.1: 75 percent / trifluoroacetic acid; acetic acid / 1 h / 100 °C
4.1: 74 percent / H2 / 10 percent Pd/C / tetrahydrofuran / 4 h / 20 °C / 3750.3 Torr
5.1: 84 percent / Na; liquid NH3 / tetrahydrofuran / 0.17 h
View Scheme

Naratriptan Chemical Properties

IUPAC name: N-Methyl-2-[3-(1-methylpiperidin-4-yl)-1H-indol-5-yl]ethanesulfonamide
Molecular Formula: C₁₇H₂₅N₃O₂S
Molecular Weight: 335.464300 g/mol
Index of Refraction: 1.605
Surface Tension: 51.3 dyne/cm
Density: 1.227 g/cm³
Flash Point: 281.2 °C
Enthalpy of Vaporization: 81.91 kJ/mol
Boiling Point: 541.3 °C at 760 mmHg
Vapour Pressure: 8.81E-12 mmHg at 25 °C
Product Categories: Indoline & Oxindole
Following is the structure of Naratriptan (CAS NO.121679-13-8):

Naratriptan Toxicity Data With Reference

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
women	TDLo	oral	3750ug/kg/22W (3.75mg/kg)	BEHAVIORAL: HEADACHE	Lancet. Vol. 353, Pg. 378, 1999.

Naratriptan Specification

Naratriptan , its cas register number is 121679-13-8. It also can be called N-Methyl-2-[3-(1-methylpiperidin-4-yl)-1H-indol-5-yl]ethanesulfonamide ; 1H-indole-5-ethanesulfonamide, N-Methyl-3-(1-methyl-4-piperidinyl)- naratriptan .
Naratriptan (trade names include Amerge and Naramig) is a triptan drug marketed by GlaxoSmithKline and is used for the treatment of migraine headaches. Naratriptan is available in 2.5 mg tablets. It is a selective 5-hydroxytryptamine1 receptor subtype agonist. Naratriptan hydrochloride is chemically designated as N-methyl-3-( 1-methyl-4-piperidinyl)-1H-indole-5-ethanesulfonamide.

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